A Novel and Stereospecific Synthesis of Conduritol-E via Cyclohexa-3,5-diene-1,2-diol

Authors: Ahmet MARAS, Hasan SECEN, Yasar SÜTBEYAZ, Metin BALCI

Abstract: Conduritol-E was synthesized starting from cyclohexa-3,5-diene-1,2-diol {\bf 1a} in six steps. Acetylation of the diol {\bf 1a} followed by bromination gave (2\alpha/1\beta, \,\, 3\beta, \,\, 4\beta)-1,2-dibromo-2,3- diacetoxy- 5-cyclohexene {\bf 3} as main product. KMnO_{4}-hydoxylation of the dibromide {\bf 3} followed by acetylation, Zn-elimination and hydrolysis afforded conduritol-E {\bf 5a}.

Keywords: cyclohexa-3,5-diene-1,2-diol, bromination, conduritol-E, conduritol-E tetraacetate.

Full Text: PDF